Pittsfield, MA Horseback Riding Trails and Maps

1037 Reviews

Looking for the best Horseback Riding trails around Pittsfield?

Find the top rated horseback riding trails in Pittsfield, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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7 Results
Activities
Length
Surfaces
Type

Mass Central Rail Trail

64 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

West River Trail (Windham County)

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Ashuelot Recreational Rail Trail

21.4 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Fort Hill Recreational Rail Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Uncle Sam Bikeway

3.1 mi
State: NY
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt
Trail Image Trail Name States Length Surface Rating
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail trail. The Mass Central Rail Trail runs for 64 miles between...
MA 64 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
VT 16.1 mi Asphalt, Dirt, Gravel, Sand
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...
NH 21.4 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
Inland and east of the Hudson River, the Uncle Sam Bike Trail (also called the Uncle Sam Trail or Uncle Sam Bikeway) largely serves as a trail for residents of Troy. If, however, you are traveling in...
NY 3.1 mi Asphalt
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
NY 3.8 mi Dirt

Recent Trail Reviews

Hoosic River Greenway

Parked in middle waked each way, nice leisurely walk.

June, 2026 by tchioc88_tl

Parked in middle waked each way, nice leisurely walk.

Farmington Canal Heritage Trail

Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.

June, 2026 by taccuosti

Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.

Zim Smith Mid-County Trail

A great ride in the Albany area! Ride in a cage!

June, 2026 by steve.schwinn

Rode this trail as an out-and-back from the Oak Street (northwest) trailhead (limited parking, no facilities). Trail is in great condition (all paved). The south/east half of the trail is the more interesting as it includes an active freight railroad crossing (I got caught!), passing adjacent to a busy freight rail yard, and riding in a cage through a golf course!
There is a portable toilet at the Coons Crossing Road trailhead (note: as of 6/2026 construction has closed the road approaching the trailhead from the north, it is open from the south).
A great ride in the Albany area!

Accordion

Ashuelot Recreational Rail Trail

pleasant ride

May, 2026 by slasalle76

I'd ridden this trail a couple years ago, doing it in small sections, and had found it to be a nice ride with a decent surface, quite reasonable for my older hybrid. I only did about 6 miles today, from Keene southward before turning back, and those couple of detours noted in another review are still in place - taking you out onto the road for short stretches likely to avoid power line work being done.

Farmington Canal Heritage Trail

Terrible Shape

May, 2026 by dave36

Rode from Avon, CT to Westfield, MA. Mass section in great shape. CT section is awful. Pavement is split, constant 'ka-thunk', pot holes not marked, just horrendous condition. Where is the CT DOT and our tax dollars? Stay away.

Valley Trail

Tough to do on a mountain bike, unless you're an expert. not maintained at all. I would say an ok hiking trail. But not all that scenic. Not what it's billed to be by a long shot.

May, 2026 by jim.thurber13

Tough to do on a mountain bike, unless you're an expert. not maintained at all. I would say an ok hiking trail. But not all that scenic. Not what it's billed to be by a long shot.

Ashuwillticook Rail Trail

Great short trail

April, 2026 by biggsfhlax

The surface is paved, and in excellent condition.
The trail is ever so slightly down hill from north to south.
Mostly shaded, and while not amazing scenery, it is a lovely trail. In spring, when sunny, watch to LOTS of turtles on the far bank of a swampy section near the cheshire reservoir (on the west side of the trail)!

Canalside Rail Trail

Beautiful scenery

November, 2025 by scanlon.gail

The Canalside rail trail is fully open and the paved trail is very well maintained. While it is only 7.2 miles round trip, it’s worth it! Plenty of parking at both ends and the town of Turners Falls has a nice selection of restaurants and shops.

Naugatuck River Greenway

Naugatuck River Greenway-Torrington CT Section(s)

October, 2025 by marieperriello86

Currently there is a couple of sections that are really nice for the work thats been completed, but will be a fantastic trail once they have completed the sections necessary to connect them into one long trail. All the sections completed are mostly all paved and are great for walking/jogging/biking & wheelchair/stroller friendly. The only exception is tgr Naugatuck River Greenway section that starts at the Sullivan Senior Center, which has a paved trail that runs parallel to the the river and ends at the side road which you continue down a one way street that almost zig zags until you reach palmer bridge. Crossing the bridge and crossing to the paved trail that goes behind a condominium and continues until the end of the dirt parking lots (trail is paved) of John Toro Sports Complex, where the pavement ends towards the actual field. Then it transitions to the field with no defined trail. The Trail at that point isnt really distinct. I lived here most of my life and I didnt know until I saw a news article about The Rainbow Bridge and found that the trail in fact extended past where the pavement ends and continues straight past the dog park past both the first baseball field, the soccer field, and then about halfway through the 2nd baseball field there is a wide opening in the forest, where you then see the entrance to the Rainbow Bridge Trail. Which is an amazing small half looped trail, with some of the most beautiful works of art, and tributes to various pets (photos, stepping stones/memorial rock garden, a memorial fence, k-9 officers memorial bulletin board(s), sculptures, poems, signs, chairs, then the rainbow Bridge which is adorned with photos, momentos, stories, collars & tributes to pets of those who came to place their beloved pets memorials. After you find the exits shortly after that you can see the wide open pathway continues for a while on but ends at a fenced off area that currently is a business/underutilized "Sports park" that will eventually be replaced with a connector trail that will connect with other nearby trails.

West River Trail (Windham County)

gorgeous fall ride

October, 2025 by darylmarlisa

We started at the marina restaurant at the south end of the trail and rode 3.5 miles on the rail trail section, with another 2 miles on Rice Farm & Quarries roads. Beautiful vistas of the river, rock formations, changing leaves. Esp impressive was the overhead highway bridge built with long tapering multicolored stone supports, representing tree branches. Under the arched stone supports is a picnic table & patio area. A few protruding stones/tree roots need to be managed but biking is very possible on this trail and should be included in the list of options for use.

Farmington Canal Heritage Trail

ok

October, 2025 by deceived

Rode a portion from Milldale north to Southington. All paved in fairly decent shape. A few bumps but no broken pavement. At the point in Southington the trail just ends with no information as to where to go. No signs or arrows. The trail picks up somewhere a few miles away but I couldn’t find out how to get there. On the portion I rode it was flat and easy, but not much to see other than woods and backs of buildings.

Valley Trail

Rode 2.5 miles from Wilmington north on mountain tire bikes and it is doable but rough with roots and rocks. Nice bridges but missing signage in some areas, others well marked. No washout areas close to Wilmington.

September, 2025 by dlonzo

Rode 2.5 miles from Wilmington north on mountain tire bikes and it is doable but rough with roots and rocks. Nice bridges but missing signage in some areas, others well marked. No washout areas close to Wilmington.

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Accordion

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